Abstract--As Large Language Models (LLMs) gain wider adoption, ensuring their reliable handling of Personally Identifiable Information (PII) across diverse regulatory contexts has become essential. This work introduces a scalable multilingual data curation framework designed for high-quality PII annotation across 13 underrepresented locales (Table I), covering approximately 336 locale-specific PII types. Our phased, human-in-the-loop annotation methodology combines linguistic expertise with rigorous quality assurance, leading to substantial improvements in recall and false positive rates from pilot, training, and production phases. Beyond reporting empirical gains, we highlight common annotator challenges in multilingual PII labeling and demonstrate how iterative, analytics-driven pipelines can enhance both annotation quality and downstream model reliability. I. Introduction A. PII Data Protection The surge in user-generated content has led to vast textual corpora containing hidden instances of Personally Identifiable Information (PII) in application forms, support tickets, reviews and social media posts [1]. PII--such as NAME, SSN, and PHONE NUMBER--poses significant privacy risks if not handled correctly. Its compromise can result in identity theft, financial fraud, and unauthorized access to sensitive data [2].

For several hours a week, I write for a technology company worth billions of dollars. Alongside me are published novelists, rising academics and several other freelance journalists. The workload is flexible, the pay better than we are used to, and the assignments never run out. But what we write will never be read by anyone outside the company. We are writing for an AI.

In this paper, we examine the work of data annotation. Specifically, we focus on the role of counting or quantification in organising annotation work. Based on an ethnographic study of data annotation in two outsourcing centres in India, we observe that counting practices and its associated logics are an integral part of day-to-day annotation activities. In particular, we call attention to the presumption of total countability observed in annotation - the notion that everything, from tasks, datasets and deliverables, to workers, work time, quality and performance, can be managed by applying the logics of counting. To examine this, we draw on sociological and socio-technical scholarship on quantification and develop the lens of a 'regime of counting' that makes explicit the specific counts, practices, actors and structures that underpin the pervasive counting in annotation. We find that within the AI supply chain and data work, counting regimes aid the assertion of authority by the AI clients (also called requesters) over annotation processes, constituting them as reductive, standardised, and homogenous. We illustrate how this has implications for i) how annotation work and workers get valued, ii) the role human discretion plays in annotation, and iii) broader efforts to introduce accountable and more just practices in AI. Through these implications, we illustrate the limits of operating within the logic of total countability. Instead, we argue for a view of counting as partial - located in distinct geographies, shaped by specific interests and accountable in only limited ways. This, we propose, sets the stage for a fundamentally different orientation to counting and what counts in data annotation.